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A kind of fipronil hapten and its synthesis method, artificial antigen, antibody and application

A synthesis method, artificial antigen technology, applied in chemical instruments and methods, animal/human proteins, instruments, etc., can solve the problems of sensitivity, specificity and precision need to be improved, and achieve high sensitivity and precision, high synthesis purity , good specificity

Active Publication Date: 2022-02-15
信达安检测技术(天津)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] When the fipronil hapten or fipronil artificial antigen prepared by the above method is used to detect fipronil by ELISA, its sensitivity, specificity and precision still need to be improved

Method used

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  • A kind of fipronil hapten and its synthesis method, artificial antigen, antibody and application
  • A kind of fipronil hapten and its synthesis method, artificial antigen, antibody and application
  • A kind of fipronil hapten and its synthesis method, artificial antigen, antibody and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] A synthetic method of fipronil hapten, comprising the following steps:

[0042] S1. Reaction of fipronil structural analogs with phenyl chloroformate to synthesize intermediate I, specifically:

[0043] Weigh 4.37g of fipronil structural analogues and dissolve in acetone, cool down in an ice bath, slowly add 1.88g of phenyl chloroformate dropwise, and then rise to 25°C to react overnight. The reaction solution was concentrated to give [5-cyano-2-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-methylsulfoxide-2H-pyrazol-3-yl]- Phenyl carbamate (Intermediate I). The intermediate I can be directly carried out in the next step without purification.

[0044] S2. reacting the intermediate I with tert-butyl allanine to synthesize the intermediate II, specifically:

[0045] Dissolve 0.50g of intermediate I in 30mL of tetrahydrofuran, add 0.01g of DBU (1,8-diazabicycloundec-7-ene), 1.21mL of triethylamine, 0.73g of tert-alanine Butyl ester, the reaction solution was heated to 65°C...

Embodiment 2

[0051] Specifically with embodiment 1, the difference is:

[0052] When synthesizing the fipronil hapten, in step S1, weigh 4.40 g of the fipronil structural analogue and dissolve it in acetone, cool down in an ice bath, slowly add 1.73 g of phenyl chloroformate dropwise, and then rise to 40° C. to react overnight.

[0053] When synthesizing the fipronil hapten, in step S2, dissolve 0.50g of intermediate I in 30mL of tetrahydrofuran, add 0.01g of DBU, 1.21mL of triethylamine, and 0.73g of tert-butyl 3-aminopropionate in sequence, and heat up the reaction solution Reaction at 50°C for 12h.

[0054] When synthesizing the fipronil hapten, in step S3, weigh 0.55 g of intermediate II and dissolve it in 10 mL of dichloromethane, add 10 mL of trifluoroacetic acid and stir at room temperature for 2 h. The purity of the synthesized fipronil hapten was 99.6%.

[0055] When synthesizing fipronil artificial antigen, weigh 10 mg of fipronil hapten and dissolve it in 200 μL of DMF, add 7....

Embodiment 3

[0057] Specifically with embodiment 1, the difference is:

[0058] When synthesizing the fipronil hapten, in step S1, weigh 4.50 g of the fipronil structural analogue and dissolve it in acetone, cool down in an ice bath, slowly add 1.61 g of phenyl chloroformate dropwise, and react overnight at 0°C.

[0059] When synthesizing the fipronil hapten, in step S2, dissolve 0.50g of intermediate I in 30mL of tetrahydrofuran, add 0.01g of DBU, 1.21mL of triethylamine, and 0.73g of tert-butyl 3-aminopropionate in sequence, and heat up the reaction solution Reaction at 80°C for 12h.

[0060] When synthesizing the fipronil hapten, in step S3, weigh 0.55 g of intermediate II and dissolve it in 15 mL of dichloromethane, add 15 mL of trifluoroacetic acid and stir at room temperature for 2 h. The purity of the synthesized fipronil hapten was 99.7%.

[0061] When synthesizing the fipronil artificial antigen, weigh 10 mg of the fipronil hapten and dissolve it in 200 μL of DMF, add 7.7 mg of ...

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Abstract

The invention discloses a fipronil hapten, a synthesis method thereof, an artificial antigen, an antibody and use thereof, and belongs to the technical field of biochemical industry. The present invention provides a fipronil hapten, and its synthesis method comprises the following steps: S1. reacting a structural analog of fipronil with phenyl chloroformate to synthesize intermediate I; S2. combining the intermediate I with an amino group Reaction with tert-butyl propionate to synthesize intermediate II; S3. De-tert-butyl of the intermediate II under acidic conditions to synthesize fipronil hapten. The artificial antigen synthesized in the present invention can retain the basic structure of fipronil to the greatest extent, and can be used to prepare antibodies with higher specificity and sensitivity. It has the advantages of good performance, high sensitivity and high precision.

Description

technical field [0001] The invention relates to a fipronil hapten and its synthesis method, artificial antigen, antibody and application, and belongs to the technical field of biochemical industry. Background technique [0002] Fipronil, trade name Fipronil, is a phenylpyrazole insecticide with a broad insecticidal spectrum. It mainly has stomach poisoning effect on pests, and also has contact killing and certain systemic effects. Its mechanism of action lies in It hinders the chloride metabolism controlled by insect γ-aminobutyric acid, so it has high insecticidal activity against important pests such as aphids, leafhoppers, planthoppers, Lepidoptera larvae, flies and Coleoptera, and has no phytotoxicity to crops. The agent can be applied to the soil or sprayed on the leaves. Applying to the soil can effectively control corn root leaf beetle, wireworm and cutworm. When sprayed on the leaves, it has a high level of control effect on diamondback moth, cabbage butterfly, ric...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/44C07K14/765C07K14/77C07K16/44G01N33/53G01N33/543G01N33/577G01N33/58
Inventor 冯艳武卫大群郭志雄葛怀娜韦吉杨仇雅婷孙惠洁
Owner 信达安检测技术(天津)有限公司
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